Ethyl 1-tert-butyl-2-(4-methoxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Abd Hamid, S.; Abdul Rahim, A.S.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810007956

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o776-o777

doi:10.1107/S1600536810007956

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Ethyl 1-tert-butyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Shafida Abd Hamid,^b Aisyah Saad Abdul Rahim,^a ‡ Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*§

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bKulliyyah of Science, International Islamic University Malaysia (IIUM), Jalan Istana, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 25 February 2010; accepted 2 March 2010; online 6 March 2010)

In the title molecule, C₂₁H₂₄N₂O₃, the imidazole ring is essentially planar, with a maxium deviation of 0.015 (1) Å. The dihedral angle between the benzene and imidazole rings is 65.47 (6)°. The crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds, forming zigzag chains along the c axis. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For background to benzimidazole derivatives, their biological activity and medical applications, see: Orjales et al. (1997 ); Andrzejewska et al. (2002 ); Garuti et al. (2000 ); Lukevics et al. (2001 ); Komazin et al. (2003 ). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ); Jeffrey (1997 ); Scheiner (1997 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₃
M_r = 352.42
Orthorhombic, P n a 2₁
a = 14.3963 (7) Å
b = 8.6206 (5) Å
c = 15.1609 (8) Å
V = 1881.54 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.53 × 0.42 × 0.27 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.957, T_max = 0.978
17426 measured reflections
4233 independent reflections
3951 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 1.13
4233 reflections
240 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the rings N1,N2,C7–C9 and C1–C6 and C8–C13, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2ⁱ	0.93	2.57	3.3822 (16)	146
C13—H13A⋯O2ⁱⁱ	0.93	2.52	3.4116 (16)	160
C19—H19C⋯N2ⁱⁱⁱ	0.96	2.57	3.4976 (19)	164
C2—H2A⋯Cg3^iv	0.93	2.75	3.5594 (14)	146
C18—H18C⋯Cg2^v	0.96	2.74	3.6878 (16)	168
C21—H21B⋯Cg1^iv	0.96	2.78	3.4703 (16)	130
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iv) x, y+1, z; (v) $[-x-{\script{1\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536810007956/wn2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007956/wn2378Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives are reported to be physiologically and pharmacologically active and find applications in the treatment of several diseases, such as epilepsy, diabetes and infertility (Orjales et al., 1997). In addition, they also show clinical benefit toward breast cancer (Andrzejewska et al., 2002), leukemia (Garuti et al., 2000), tumor cells (Lukevics et al., 2001) and possess potent antiviral activities (Komazin et al., 2003). We present here the crystal structure of the title compound.

In the asymmetric unit of the title compound (Fig. 1), the imidazole ring is essentially planar, with a maximum deviation of 0.015 (1) Å for atom C8. The dihedral angle between the imidazole ring (N1/N2/C7–C9) and the benzene ring (C1–C6) is 65.47 (6)° .

In the crystal structure (Fig. 2), neighbouring molecules are connected by weak intermolecular C5—H5A···O2, C13—H13A···O2 and C19—H19C···N2 hydrogen bonds (Jeffrey & Saenger, 1991; Jeffrey, 1997; Scheiner, 1997), forming zigzag chains along the c-axis. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the N1/N2/C7–C9 (centroid Cg1), C1–C6 (centroid Cg2) and C8–C13 (centroid Cg3) rings.

Related literature top

For background to benzimidazole derivatives, their biological activity and medical applications, see: Orjales et al. (1997); Andrzejewska et al. (2002); Garuti et al. (2000); Lukevics et al. (2001); Komazin et al. (2003). For details of hydrogen bonding see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl-3-amino-4-(tert-butylamino) benzoate (200 mg, 0.84 mmol) and the sodium metabisulfite adduct of 4-methoxybenzaldehyde (406 mg, 1.68 mmol) were dissolved in DMF. The reaction mixture was irradiated under microwave conditions at 130 °C for 2 minutes. After completion, the reaction mixture was diluted in EtOAc (20 ml) and washed with H₂O (20 ml). The organic layer was collected, dried over Na₂SO₄ and then evaporated in vacuo to yield the crude product. The product was recrystallised from EtOAc as colourless crystals.

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound, showing the hydrogen-bonded (dashed lines) network. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

Ethyl 1-tert-butyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₁H₂₄N₂O₃	F(000) = 752
M_r = 352.42	D_x = 1.244 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6765 reflections
a = 14.3963 (7) Å	θ = 2.7–36.9°
b = 8.6206 (5) Å	µ = 0.08 mm⁻¹
c = 15.1609 (8) Å	T = 100 K
V = 1881.54 (17) Å³	Block, colourless
Z = 4	0.53 × 0.42 × 0.27 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	3951 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 35.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→12
T_min = 0.957, T_max = 0.978	k = −12→13
17426 measured reflections	l = −24→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0773P)²] where P = (F_o² + 2F_c²)/3
4233 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.60 e Å⁻³
1 restraint	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₃	V = 1881.54 (17) Å³
M_r = 352.42	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.3963 (7) Å	µ = 0.08 mm⁻¹
b = 8.6206 (5) Å	T = 100 K
c = 15.1609 (8) Å	0.53 × 0.42 × 0.27 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4233 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3951 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.978	R_int = 0.032
17426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.113	H-atom parameters constrained
S = 1.13	Δρ_max = 0.60 e Å⁻³
4233 reflections	Δρ_min = −0.57 e Å⁻³
240 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.12374 (8)	1.21773 (11)	0.18521 (7)	0.02061 (19)
O2	0.25619 (7)	0.09272 (11)	0.59077 (8)	0.02019 (19)
O3	0.11256 (7)	0.01389 (12)	0.63146 (8)	0.02132 (19)
N1	0.00387 (7)	0.60189 (11)	0.40798 (7)	0.01307 (17)
N2	0.16125 (7)	0.58244 (12)	0.40296 (7)	0.01439 (18)
C1	0.07671 (9)	0.95165 (14)	0.37017 (8)	0.0159 (2)
H1A	0.0560	0.9522	0.4283	0.019*
C2	0.08488 (9)	1.09163 (14)	0.32461 (9)	0.0158 (2)
H2A	0.0694	1.1849	0.3518	0.019*
C3	0.11669 (9)	1.08946 (13)	0.23757 (8)	0.01465 (19)
C4	0.14432 (9)	0.95031 (14)	0.19836 (8)	0.0156 (2)
H4A	0.1685	0.9503	0.1415	0.019*
C5	0.13556 (8)	0.81218 (14)	0.24449 (8)	0.01461 (19)
H5A	0.1541	0.7195	0.2184	0.018*
C6	0.09897 (8)	0.81128 (13)	0.33013 (8)	0.01312 (18)
C7	0.08802 (8)	0.66340 (14)	0.37851 (8)	0.01293 (19)
C8	0.02836 (8)	0.47467 (13)	0.45937 (8)	0.01276 (18)
C9	0.12598 (8)	0.46271 (13)	0.45378 (8)	0.01270 (18)
C10	0.17417 (8)	0.34437 (14)	0.49659 (8)	0.01382 (19)
H10A	0.2384	0.3360	0.4921	0.017*
C11	0.12284 (8)	0.23910 (13)	0.54632 (8)	0.01365 (18)
C12	0.02572 (8)	0.25487 (14)	0.55447 (8)	0.0156 (2)
H12A	−0.0068	0.1845	0.5892	0.019*
C13	−0.02274 (8)	0.37223 (14)	0.51221 (8)	0.0157 (2)
H13A	−0.0867	0.3826	0.5187	0.019*
C14	0.17224 (8)	0.10981 (14)	0.59068 (9)	0.01472 (19)
C15	0.14999 (11)	−0.12009 (16)	0.67719 (10)	0.0227 (2)
H15A	0.1157	−0.1375	0.7314	0.027*
H15B	0.2145	−0.1017	0.6923	0.027*
C16	0.14263 (14)	−0.26002 (18)	0.61893 (12)	0.0300 (3)
H16A	0.1631	−0.3501	0.6507	0.045*
H16B	0.1809	−0.2458	0.5677	0.045*
H16C	0.0792	−0.2738	0.6010	0.045*
C17	−0.09468 (8)	0.64670 (15)	0.38647 (9)	0.0157 (2)
C18	−0.14919 (10)	0.50058 (19)	0.36114 (13)	0.0279 (3)
H18A	−0.1544	0.4337	0.4115	0.042*
H18B	−0.1172	0.4471	0.3146	0.042*
H18C	−0.2101	0.5294	0.3414	0.042*
C19	−0.13666 (11)	0.7233 (2)	0.46773 (11)	0.0290 (3)
H19A	−0.0993	0.8106	0.4846	0.044*
H19B	−0.1386	0.6499	0.5153	0.044*
H19C	−0.1985	0.7578	0.4545	0.044*
C20	−0.10132 (11)	0.7557 (2)	0.30761 (12)	0.0305 (4)
H20A	−0.0752	0.8545	0.3229	0.046*
H20B	−0.1653	0.7688	0.2914	0.046*
H20C	−0.0677	0.7124	0.2588	0.046*
C21	0.09176 (12)	1.36157 (16)	0.22065 (10)	0.0232 (3)
H21A	0.0965	1.4409	0.1765	0.035*
H21B	0.1291	1.3894	0.2707	0.035*
H21C	0.0281	1.3511	0.2387	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0309 (5)	0.0144 (4)	0.0165 (4)	−0.0019 (3)	0.0026 (4)	0.0018 (3)
O2	0.0146 (4)	0.0221 (4)	0.0239 (4)	0.0031 (3)	−0.0012 (3)	0.0034 (4)
O3	0.0189 (4)	0.0182 (4)	0.0269 (5)	0.0009 (3)	0.0004 (4)	0.0079 (4)
N1	0.0101 (4)	0.0151 (4)	0.0141 (4)	0.0004 (3)	0.0000 (3)	0.0013 (3)
N2	0.0117 (4)	0.0141 (4)	0.0174 (4)	−0.0014 (3)	0.0000 (3)	0.0012 (3)
C1	0.0196 (5)	0.0144 (5)	0.0138 (5)	−0.0004 (4)	0.0016 (4)	−0.0007 (4)
C2	0.0195 (5)	0.0135 (5)	0.0145 (5)	−0.0007 (4)	0.0013 (4)	−0.0010 (4)
C3	0.0165 (5)	0.0137 (4)	0.0137 (5)	−0.0022 (4)	−0.0007 (4)	−0.0003 (4)
C4	0.0172 (5)	0.0162 (5)	0.0134 (5)	−0.0025 (4)	0.0015 (4)	−0.0012 (4)
C5	0.0140 (4)	0.0142 (4)	0.0156 (5)	−0.0008 (4)	0.0012 (4)	−0.0019 (4)
C6	0.0126 (4)	0.0127 (4)	0.0140 (4)	−0.0014 (3)	−0.0001 (4)	0.0000 (4)
C7	0.0114 (4)	0.0134 (4)	0.0140 (5)	−0.0009 (3)	−0.0008 (3)	−0.0013 (4)
C8	0.0105 (4)	0.0142 (4)	0.0136 (4)	−0.0001 (3)	0.0007 (3)	0.0006 (4)
C9	0.0102 (4)	0.0130 (4)	0.0149 (4)	−0.0006 (3)	−0.0001 (3)	0.0000 (3)
C10	0.0101 (4)	0.0142 (4)	0.0172 (5)	0.0002 (3)	−0.0010 (4)	−0.0003 (4)
C11	0.0128 (4)	0.0140 (4)	0.0142 (4)	0.0012 (3)	−0.0004 (4)	0.0000 (4)
C12	0.0127 (4)	0.0170 (5)	0.0170 (5)	0.0005 (4)	0.0017 (4)	0.0030 (4)
C13	0.0113 (4)	0.0181 (5)	0.0177 (5)	0.0007 (4)	0.0016 (4)	0.0028 (4)
C14	0.0151 (5)	0.0143 (4)	0.0147 (5)	0.0008 (3)	−0.0012 (4)	−0.0005 (4)
C15	0.0261 (6)	0.0183 (5)	0.0236 (6)	0.0020 (5)	−0.0020 (5)	0.0058 (5)
C16	0.0397 (8)	0.0215 (6)	0.0288 (7)	0.0028 (6)	0.0070 (6)	−0.0002 (5)
C17	0.0101 (4)	0.0204 (5)	0.0165 (5)	0.0025 (4)	−0.0005 (4)	0.0039 (4)
C18	0.0166 (5)	0.0265 (6)	0.0407 (8)	−0.0035 (5)	−0.0102 (5)	0.0018 (6)
C19	0.0214 (6)	0.0409 (8)	0.0248 (7)	0.0142 (6)	0.0012 (5)	−0.0047 (6)
C20	0.0176 (6)	0.0428 (9)	0.0310 (8)	−0.0059 (6)	−0.0073 (5)	0.0231 (7)
C21	0.0339 (7)	0.0139 (5)	0.0220 (6)	0.0002 (5)	0.0013 (5)	0.0024 (4)

Geometric parameters (Å, º) top

O1—C3	1.3649 (15)	C11—C12	1.4102 (16)
O1—C21	1.4277 (17)	C11—C14	1.4833 (16)
O2—C14	1.2174 (15)	C12—C13	1.3860 (16)
O3—C14	1.3432 (16)	C12—H12A	0.9300
O3—C15	1.4509 (16)	C13—H13A	0.9300
N1—C8	1.3908 (15)	C15—C16	1.499 (2)
N1—C7	1.3958 (15)	C15—H15A	0.9700
N1—C17	1.5061 (15)	C15—H15B	0.9700
N2—C7	1.3176 (15)	C16—H16A	0.9600
N2—C9	1.3845 (15)	C16—H16B	0.9600
C1—C6	1.3912 (16)	C16—H16C	0.9600
C1—C2	1.3954 (17)	C17—C19	1.523 (2)
C1—H1A	0.9300	C17—C20	1.5236 (19)
C2—C3	1.3970 (18)	C17—C18	1.5330 (19)
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.3966 (17)	C18—H18B	0.9600
C4—C5	1.3868 (16)	C18—H18C	0.9600
C4—H4A	0.9300	C19—H19A	0.9600
C5—C6	1.4011 (17)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.4792 (16)	C20—H20A	0.9600
C8—C13	1.4010 (16)	C20—H20B	0.9600
C8—C9	1.4117 (15)	C20—H20C	0.9600
C9—C10	1.3941 (16)	C21—H21A	0.9600
C10—C11	1.3921 (16)	C21—H21B	0.9600
C10—H10A	0.9300	C21—H21C	0.9600

C3—O1—C21	117.44 (11)	O2—C14—O3	124.05 (11)
C14—O3—C15	118.20 (11)	O2—C14—C11	124.57 (11)
C8—N1—C7	105.00 (9)	O3—C14—C11	111.38 (10)
C8—N1—C17	124.22 (9)	O3—C15—C16	109.43 (13)
C7—N1—C17	130.60 (10)	O3—C15—H15A	109.8
C7—N2—C9	104.95 (10)	C16—C15—H15A	109.8
C6—C1—C2	121.12 (11)	O3—C15—H15B	109.8
C6—C1—H1A	119.4	C16—C15—H15B	109.8
C2—C1—H1A	119.4	H15A—C15—H15B	108.2
C1—C2—C3	118.93 (11)	C15—C16—H16A	109.5
C1—C2—H2A	120.5	C15—C16—H16B	109.5
C3—C2—H2A	120.5	H16A—C16—H16B	109.5
O1—C3—C4	115.29 (11)	C15—C16—H16C	109.5
O1—C3—C2	124.26 (11)	H16A—C16—H16C	109.5
C4—C3—C2	120.46 (11)	H16B—C16—H16C	109.5
C5—C4—C3	119.80 (11)	N1—C17—C19	108.05 (11)
C5—C4—H4A	120.1	N1—C17—C20	112.78 (10)
C3—C4—H4A	120.1	C19—C17—C20	110.03 (13)
C4—C5—C6	120.42 (11)	N1—C17—C18	109.01 (10)
C4—C5—H5A	119.8	C19—C17—C18	110.85 (13)
C6—C5—H5A	119.8	C20—C17—C18	106.14 (12)
C1—C6—C5	119.08 (11)	C17—C18—H18A	109.5
C1—C6—C7	120.58 (10)	C17—C18—H18B	109.5
C5—C6—C7	120.29 (10)	H18A—C18—H18B	109.5
N2—C7—N1	113.78 (10)	C17—C18—H18C	109.5
N2—C7—C6	120.71 (10)	H18A—C18—H18C	109.5
N1—C7—C6	125.36 (10)	H18B—C18—H18C	109.5
N1—C8—C13	133.18 (10)	C17—C19—H19A	109.5
N1—C8—C9	106.04 (10)	C17—C19—H19B	109.5
C13—C8—C9	120.74 (10)	H19A—C19—H19B	109.5
N2—C9—C10	128.47 (10)	C17—C19—H19C	109.5
N2—C9—C8	110.13 (10)	H19A—C19—H19C	109.5
C10—C9—C8	121.39 (10)	H19B—C19—H19C	109.5
C11—C10—C9	117.71 (10)	C17—C20—H20A	109.5
C11—C10—H10A	121.1	C17—C20—H20B	109.5
C9—C10—H10A	121.1	H20A—C20—H20B	109.5
C10—C11—C12	120.73 (10)	C17—C20—H20C	109.5
C10—C11—C14	118.74 (10)	H20A—C20—H20C	109.5
C12—C11—C14	120.53 (10)	H20B—C20—H20C	109.5
C13—C12—C11	121.94 (11)	O1—C21—H21A	109.5
C13—C12—H12A	119.0	O1—C21—H21B	109.5
C11—C12—H12A	119.0	H21A—C21—H21B	109.5
C12—C13—C8	117.39 (10)	O1—C21—H21C	109.5
C12—C13—H13A	121.3	H21A—C21—H21C	109.5
C8—C13—H13A	121.3	H21B—C21—H21C	109.5

C6—C1—C2—C3	−0.48 (19)	C7—N2—C9—C8	−0.18 (13)
C21—O1—C3—C4	176.78 (12)	N1—C8—C9—N2	2.09 (13)
C21—O1—C3—C2	−3.48 (19)	C13—C8—C9—N2	−175.77 (11)
C1—C2—C3—O1	177.04 (12)	N1—C8—C9—C10	−178.71 (11)
C1—C2—C3—C4	−3.22 (18)	C13—C8—C9—C10	3.43 (18)
O1—C3—C4—C5	−176.84 (11)	N2—C9—C10—C11	178.14 (12)
C2—C3—C4—C5	3.40 (18)	C8—C9—C10—C11	−0.90 (18)
C3—C4—C5—C6	0.13 (18)	C9—C10—C11—C12	−1.53 (18)
C2—C1—C6—C5	3.95 (18)	C9—C10—C11—C14	178.49 (11)
C2—C1—C6—C7	−178.63 (11)	C10—C11—C12—C13	1.53 (19)
C4—C5—C6—C1	−3.76 (17)	C14—C11—C12—C13	−178.48 (12)
C4—C5—C6—C7	178.81 (11)	C11—C12—C13—C8	0.94 (19)
C9—N2—C7—N1	−1.88 (14)	N1—C8—C13—C12	179.47 (12)
C9—N2—C7—C6	173.81 (11)	C9—C8—C13—C12	−3.35 (18)
C8—N1—C7—N2	3.19 (14)	C15—O3—C14—O2	−1.2 (2)
C17—N1—C7—N2	−172.05 (11)	C15—O3—C14—C11	179.23 (11)
C8—N1—C7—C6	−172.26 (11)	C10—C11—C14—O2	4.03 (19)
C17—N1—C7—C6	12.49 (19)	C12—C11—C14—O2	−175.95 (13)
C1—C6—C7—N2	−110.78 (14)	C10—C11—C14—O3	−176.36 (11)
C5—C6—C7—N2	66.61 (15)	C12—C11—C14—O3	3.65 (16)
C1—C6—C7—N1	64.39 (16)	C14—O3—C15—C16	−97.76 (15)
C5—C6—C7—N1	−118.22 (13)	C8—N1—C17—C19	76.40 (15)
C7—N1—C8—C13	174.46 (13)	C7—N1—C17—C19	−109.15 (15)
C17—N1—C8—C13	−9.9 (2)	C8—N1—C17—C20	−161.76 (13)
C7—N1—C8—C9	−3.02 (12)	C7—N1—C17—C20	12.69 (19)
C17—N1—C8—C9	172.61 (11)	C8—N1—C17—C18	−44.15 (16)
C7—N2—C9—C10	−179.31 (12)	C7—N1—C17—C18	130.30 (14)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the rings N1,N2,C7–C9 and C1–C6 and C8–C13, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2ⁱ	0.93	2.57	3.3822 (16)	146
C13—H13A···O2ⁱⁱ	0.93	2.52	3.4116 (16)	160
C19—H19C···N2ⁱⁱⁱ	0.96	2.57	3.4976 (19)	164
C2—H2A···Cg3^iv	0.93	2.75	3.5594 (14)	146
C18—H18C···Cg2^v	0.96	2.74	3.6878 (16)	168
C21—H21B···Cg1^iv	0.96	2.78	3.4703 (16)	130

Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z; (iii) x−1/2, −y+3/2, z; (iv) x, y+1, z; (v) −x−1/2, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₃
M_r	352.42
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	14.3963 (7), 8.6206 (5), 15.1609 (8)
V (Å³)	1881.54 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.53 × 0.42 × 0.27

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.957, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	17426, 4233, 3951
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.113, 1.13
No. of reflections	4233
No. of parameters	240
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.57

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the rings N1,N2,C7–C9 and C1–C6 and C8–C13, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2ⁱ	0.9300	2.5700	3.3822 (16)	146.00
C13—H13A···O2ⁱⁱ	0.9300	2.5200	3.4116 (16)	160.00
C19—H19C···N2ⁱⁱⁱ	0.9600	2.5700	3.4976 (19)	164.00
C2—H2A···Cg3^iv	0.9300	2.7500	3.5594 (14)	146.00
C18—H18C···Cg2^v	0.9600	2.7400	3.6878 (16)	168.00
C21—H21B···Cg1^iv	0.9600	2.7800	3.4703 (16)	130.00

Symmetry codes: (i) −x+1/2, y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z; (iii) x−1/2, −y+3/2, z; (iv) x, y+1, z; (v) −x−1/2, y+3/2, z+1/2.

Footnotes

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

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NA, SAH and ASAR are grateful to Universiti Sains Malaysia (USM) and the International Islamic University Malaysia (IIUM) for funding the synthetic chemistry work under the USM Research University Grant (1001/PFARMASI/815026) and the IIUM Research Endowment Grant (EDW B 0902-206). NA thanks USM for the award of a post-doctoral fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks USM for a post-doctoral research fellowship.

References

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Volume 66| Part 4| April 2010| Pages o776-o777

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