Ethyl 1-(butan-2-yl)-2-(2-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Ngah, N.; Osman, H.; Abdul Rahim, A.S.

doi:10.1107/S1600536811046095

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3231-o3232

https://doi.org/10.1107/S1600536811046095

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Ethyl 1-(butan-2-yl)-2-(2-methoxyphenyl)-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Nurziana Ngah,^b Hasnah Osman ^c and Aisyah Saad Abdul Rahim ^a ^*

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM Penang, Malaysia, ^bKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia, and ^cSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM Penang, Malaysia
^*Correspondence e-mail: aisyah@usm.my

(Received 17 October 2011; accepted 2 November 2011; online 9 November 2011)

In the title compound, C₂₁H₂₄N₂O₃, the mean planes of the benzene ring and the benzimidazole ring system form a dihedral angle of 69.94 (7)°. The ethyl group atoms of the ethanoate fragment are disordered over two sets of sites, with refined occupancies of 0.742 (6) and 0.258 (6). In the crystal, there are weak C—H⋯N hydrogen bonds which connect molecules into chains along the b axis. A weak intermolecular C—H⋯π interaction is also observed.

Related literature

For the synthesis and a closely related structure, see: Arumugam et al. (2010 ). For background to microwave chemistry, see: Kappe & Dallinger (2006 ); Hamzah et al. (2011 ). For the synthesis of benzimidazole derivatives and their applications, see: Wang et al. (2011 ); VanVliet et al. (2005 ); Loupy (2002 ); Santagada et al. (2001 ); Nicolaou et al. (2000 ); Evans et al. (1988 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₃
M_r = 352.42
Monoclinic, P 2₁ /n
a = 10.6746 (3) Å
b = 12.3344 (4) Å
c = 15.6158 (5) Å
β = 106.901 (1)°
V = 1967.25 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.52 × 0.44 × 0.32 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.959, T_max = 0.975
17688 measured reflections
3475 independent reflections
2712 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.05
3475 reflections
245 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/N2/C1/C2/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N1ⁱ	0.93	2.56	3.471 (2)	165
C20A—H20C⋯Cgⁱⁱ	0.97	2.90	3.71 (4)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+2, -z+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/S1600536811046095/lh5357sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046095/lh5357Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046095/lh5357Isup3.cml

checkCIF report

Comment top

Microwave-assisted synthesis of heterocycles proves to be an invaluable technology in the fields of medicinal chemistry and drug discovery (Kappe & Dallinger, 2006). The utility of high-speed microwave chemistry is evident from the reported synthesis of privileged structures (Evans et al., 1988; Nicolaou et al., 2000) such as benzodiazepine (Santagada et al., 2001), indoles (Loupy, 2002) and benzimidazoles (Wang et al., 2011; VanVliet et al., 2005). As a part of our on-going work in benzimidazole synthesis under microwave conditions (Hamzah et al., 2011), we present herein the X-ray crystal structure of the title compound.

The molecular structure of the title compound (Fig. 1) is similiar to the previously reported ethyl 1-sec-butyl-2-(4-methoxyphenyl) -1H-benzimidazole-5-carboxylate (Arumugam et al., 2010) in that only the position of the methoxy group is different. The benzene [C8—C13] ring and benzimidazole ring system [N1/N2/C1-C7] are essentially planar with maximum deviation of 0.050 (1)Å for atom N2. The mean-planes of the rings form a dihedral angle of 69.94 (7)°. The bond lengths (Allen et al., 1987) and angles aree in the normal ranges and comparable to those in para-methoxy derivative. The ethyl atoms (C20 & C21) of ethanoate fragment are disordered over two positions with refined site occupancies of 0.742 (6) and 0.258 (6). In the crystal, a C12—H12···N1ⁱ hydrogen bond connects molecules to form a zigzag chain propagating along the b axis (Fig. 2). An weak intermolecular C20A—H20C···Cgⁱⁱ (minor component of disorder) interaction is also observed; Cg1 is the centroid of N1/N2/C1/C2/C7.

Related literature top

For the synthesis and a closely related structure, see: Arumugam et al. (2010). For background to microwave chemistry, see: Kappe & Dallinger (2006); Hamzah et al. (2011). For the synthesis of benzimidazole derivatives and their applications, see: Wang et al. (2011); VanVliet et al. (2005); Loupy (2002); Santagada et al. (2001); Nicolaou et al. (2000); Evans et al. (1988). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to our previous procedure (Arumugam et al., 2010). A solution of the sec-butyl phenylene diamine (1.0 mmol) and sodium bisulfite adduct of 2-methoxybenzaldehyde (3.5 mmol) in DMF was heated under focused microwave conditions at 403K for 2 minutes. The reaction mixture was diluted in EtOAc (20 ml) and washed with H₂O (20 ml). The organic layer was pooled together, dried over Na₂SO₄, and then removed in vacuo. Recrystallization with ethyl acetate gave the title compound as colourless crystals.

Structure description top

For the synthesis and a closely related structure, see: Arumugam et al. (2010). For background to microwave chemistry, see: Kappe & Dallinger (2006); Hamzah et al. (2011). For the synthesis of benzimidazole derivatives and their applications, see: Wang et al. (2011); VanVliet et al. (2005); Loupy (2002); Santagada et al. (2001); Nicolaou et al. (2000); Evans et al. (1988). For standard bond lengths, see: Allen et al. (1987).

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 (I) with displacement ellipsods are drawn at the 40% probability level. Both disordered component are shown, atoms label with suffix A correspond to minor disorder component.
	Fig. 2. The molecular packing of (I) viewed along the a axis.

Ethyl 1-(butan-2-yl)-2-(2-methoxyphenyl)-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₁H₂₄N₂O₃	F(000) = 752
M_r = 352.42	D_x = 1.190 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8039 reflections
a = 10.6746 (3) Å	θ = 2.1–25.0°
b = 12.3344 (4) Å	µ = 0.08 mm⁻¹
c = 15.6158 (5) Å	T = 296 K
β = 106.901 (1)°	Block, colourless
V = 1967.25 (11) Å³	0.52 × 0.44 × 0.32 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	2712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
φ and ω scan	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→14
T_min = 0.959, T_max = 0.975	l = −18→17
17688 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0526P)² + 0.5324P] where P = (F_o² + 2F_c²)/3
3475 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.35 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₃	V = 1967.25 (11) Å³
M_r = 352.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6746 (3) Å	µ = 0.08 mm⁻¹
b = 12.3344 (4) Å	T = 296 K
c = 15.6158 (5) Å	0.52 × 0.44 × 0.32 mm
β = 106.901 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3475 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2712 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.975	R_int = 0.025
17688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
3475 reflections	Δρ_min = −0.18 e Å⁻³
245 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	Occ. (<1)
O1	0.22019 (14)	0.60261 (11)	0.83252 (9)	0.0694 (4)
O2	0.16647 (18)	1.12078 (12)	1.21044 (10)	0.0894 (5)
O3	0.10964 (19)	1.17279 (12)	1.06857 (10)	0.0917 (5)
N1	0.29480 (16)	0.88252 (11)	0.90695 (9)	0.0562 (4)
N2	0.36352 (14)	0.74369 (11)	1.00207 (8)	0.0475 (3)
C1	0.34617 (16)	0.78558 (13)	0.91776 (10)	0.0467 (4)
C2	0.32104 (16)	0.82294 (12)	1.04995 (10)	0.0445 (4)
C3	0.31600 (18)	0.82949 (14)	1.13790 (11)	0.0551 (5)
H3	0.3450	0.7729	1.1781	0.066*
C4	0.26638 (18)	0.92316 (14)	1.16254 (11)	0.0542 (4)
H4	0.2638	0.9304	1.2213	0.065*
C5	0.21963 (17)	1.00806 (13)	1.10246 (11)	0.0496 (4)
C6	0.22494 (19)	1.00099 (13)	1.01515 (11)	0.0540 (5)
H6	0.1942	1.0572	0.9748	0.065*
C7	0.27727 (17)	0.90788 (13)	0.98941 (10)	0.0473 (4)
C8	0.38804 (17)	0.72852 (14)	0.84697 (10)	0.0498 (4)
C9	0.49117 (19)	0.76994 (16)	0.82051 (12)	0.0606 (5)
H9	0.5345	0.8316	0.8484	0.073*
C10	0.5308 (2)	0.72096 (19)	0.75319 (13)	0.0711 (6)
H10	0.6003	0.7493	0.7358	0.085*
C11	0.4666 (2)	0.63017 (18)	0.71234 (13)	0.0694 (6)
H11	0.4939	0.5966	0.6675	0.083*
C12	0.3627 (2)	0.58773 (16)	0.73630 (11)	0.0608 (5)
H12	0.3196	0.5264	0.7076	0.073*
C13	0.32254 (18)	0.63726 (14)	0.80372 (11)	0.0517 (4)
C14	0.1359 (2)	0.52171 (19)	0.78162 (15)	0.0819 (6)
H14A	0.0981	0.5473	0.7216	0.123*
H14B	0.0675	0.5063	0.8084	0.123*
H14C	0.1852	0.4569	0.7805	0.123*
C15	0.42814 (19)	0.63962 (14)	1.03579 (12)	0.0601 (5)
H15	0.4483	0.6042	0.9852	0.072*
C16	0.3357 (2)	0.56259 (16)	1.06687 (15)	0.0782 (6)
H16A	0.3108	0.5957	1.1151	0.117*
H16B	0.3800	0.4955	1.0869	0.117*
H16C	0.2589	0.5488	1.0179	0.117*
C17	0.5563 (2)	0.65788 (19)	1.10606 (15)	0.0816 (6)
H17A	0.5395	0.6900	1.1583	0.098*
H17B	0.5984	0.5884	1.1238	0.098*
C18	0.6475 (2)	0.7294 (2)	1.07565 (18)	0.1013 (8)
H18A	0.6583	0.7017	1.0208	0.152*
H18B	0.7308	0.7312	1.1206	0.152*
H18C	0.6120	0.8014	1.0660	0.152*
C19	0.1636 (2)	1.10442 (15)	1.13428 (13)	0.0599 (5)
C20	0.0550 (11)	1.2722 (4)	1.0931 (10)	0.103 (2)	0.742 (6)
H20A	−0.0207	1.2560	1.1134	0.124*	0.742 (6)
H20B	0.1196	1.3091	1.1409	0.124*	0.742 (6)
C21	0.0176 (5)	1.3391 (3)	1.0141 (4)	0.1145 (15)	0.742 (6)
H21A	−0.0225	1.4045	1.0269	0.172*	0.742 (6)
H21B	−0.0436	1.3005	0.9667	0.172*	0.742 (6)
H21C	0.0938	1.3571	0.9963	0.172*	0.742 (6)
C21A	0.0967 (16)	1.3540 (11)	1.0711 (11)	0.1145 (15)	0.258 (6)
H21D	0.0569	1.4175	1.0873	0.172*	0.258 (6)
H21E	0.0936	1.3581	1.0091	0.172*	0.258 (6)
H21F	0.1863	1.3495	1.1073	0.172*	0.258 (6)
C20A	0.027 (4)	1.2591 (10)	1.086 (3)	0.103 (2)	0.258 (6)
H20C	−0.0605	1.2561	1.0439	0.124*	0.258 (6)
H20D	0.0210	1.2562	1.1463	0.124*	0.258 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0819 (9)	0.0691 (9)	0.0610 (8)	−0.0156 (7)	0.0268 (7)	−0.0184 (6)
O2	0.1453 (15)	0.0707 (10)	0.0661 (9)	0.0110 (9)	0.0526 (10)	−0.0165 (7)
O3	0.1471 (15)	0.0615 (9)	0.0743 (10)	0.0397 (9)	0.0445 (10)	−0.0029 (8)
N1	0.0877 (11)	0.0440 (8)	0.0398 (8)	0.0137 (7)	0.0233 (7)	0.0026 (6)
N2	0.0624 (9)	0.0405 (7)	0.0401 (7)	0.0093 (6)	0.0158 (6)	0.0030 (6)
C1	0.0582 (10)	0.0426 (9)	0.0392 (9)	0.0031 (8)	0.0140 (7)	−0.0008 (7)
C2	0.0558 (10)	0.0399 (9)	0.0390 (9)	0.0005 (7)	0.0158 (7)	0.0000 (7)
C3	0.0745 (12)	0.0514 (10)	0.0420 (9)	0.0053 (9)	0.0212 (8)	0.0077 (8)
C4	0.0724 (12)	0.0558 (11)	0.0394 (9)	−0.0028 (9)	0.0243 (8)	−0.0021 (8)
C5	0.0639 (11)	0.0422 (9)	0.0473 (10)	−0.0050 (8)	0.0233 (8)	−0.0073 (7)
C6	0.0795 (12)	0.0391 (9)	0.0451 (10)	0.0076 (8)	0.0207 (9)	0.0020 (7)
C7	0.0662 (11)	0.0398 (9)	0.0377 (9)	0.0034 (8)	0.0179 (8)	−0.0004 (7)
C8	0.0630 (11)	0.0465 (10)	0.0396 (9)	0.0106 (8)	0.0146 (8)	−0.0004 (7)
C9	0.0673 (12)	0.0607 (12)	0.0557 (11)	0.0019 (9)	0.0206 (9)	−0.0064 (9)
C10	0.0667 (12)	0.0876 (15)	0.0654 (12)	0.0048 (11)	0.0291 (10)	−0.0104 (11)
C11	0.0724 (13)	0.0841 (15)	0.0542 (11)	0.0195 (11)	0.0224 (10)	−0.0142 (10)
C12	0.0739 (13)	0.0579 (11)	0.0455 (10)	0.0130 (10)	0.0093 (9)	−0.0108 (8)
C13	0.0608 (11)	0.0507 (10)	0.0417 (9)	0.0078 (8)	0.0118 (8)	−0.0020 (8)
C14	0.0747 (14)	0.0818 (15)	0.0828 (15)	−0.0122 (12)	0.0129 (11)	−0.0203 (12)
C15	0.0793 (13)	0.0460 (10)	0.0529 (11)	0.0168 (9)	0.0158 (9)	0.0044 (8)
C16	0.1111 (18)	0.0497 (11)	0.0806 (14)	0.0041 (11)	0.0386 (13)	0.0131 (10)
C17	0.0878 (15)	0.0715 (14)	0.0733 (14)	0.0173 (11)	0.0039 (11)	0.0000 (11)
C18	0.0757 (16)	0.101 (2)	0.111 (2)	−0.0132 (13)	0.0018 (13)	−0.0121 (15)
C19	0.0810 (13)	0.0475 (10)	0.0584 (12)	−0.0050 (9)	0.0315 (10)	−0.0091 (9)
C20	0.153 (6)	0.058 (2)	0.108 (4)	0.034 (3)	0.053 (5)	−0.011 (2)
C21	0.117 (4)	0.081 (2)	0.142 (4)	0.041 (3)	0.031 (3)	0.006 (3)
C21A	0.117 (4)	0.081 (2)	0.142 (4)	0.041 (3)	0.031 (3)	0.006 (3)
C20A	0.153 (6)	0.058 (2)	0.108 (4)	0.034 (3)	0.053 (5)	−0.011 (2)

Geometric parameters (Å, º) top

O1—C13	1.365 (2)	C12—C13	1.388 (2)
O1—C14	1.422 (2)	C12—H12	0.9300
O2—C19	1.198 (2)	C14—H14A	0.9600
O3—C19	1.324 (2)	C14—H14B	0.9600
O3—C20A	1.456 (5)	C14—H14C	0.9600
O3—C20	1.456 (4)	C15—C17	1.501 (3)
N1—C1	1.306 (2)	C15—C16	1.546 (3)
N1—C7	1.390 (2)	C15—H15	0.9800
N2—C1	1.376 (2)	C16—H16A	0.9600
N2—C2	1.385 (2)	C16—H16B	0.9600
N2—C15	1.480 (2)	C16—H16C	0.9600
C1—C8	1.485 (2)	C17—C18	1.489 (3)
C2—C3	1.392 (2)	C17—H17A	0.9700
C2—C7	1.397 (2)	C17—H17B	0.9700
C3—C4	1.372 (2)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.398 (2)	C18—H18C	0.9600
C4—H4	0.9300	C20—C21	1.441 (12)
C5—C6	1.384 (2)	C20—H20A	0.9700
C5—C19	1.480 (2)	C20—H20B	0.9700
C6—C7	1.387 (2)	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C8—C9	1.381 (3)	C21—H21C	0.9600
C8—C13	1.392 (2)	C21A—C20A	1.440 (13)
C9—C10	1.381 (3)	C21A—H21D	0.9600
C9—H9	0.9300	C21A—H21E	0.9600
C10—C11	1.370 (3)	C21A—H21F	0.9600
C10—H10	0.9300	C20A—H20C	0.9700
C11—C12	1.373 (3)	C20A—H20D	0.9700
C11—H11	0.9300

C13—O1—C14	118.20 (15)	N2—C15—C17	111.19 (16)
C19—O3—C20A	118.4 (17)	N2—C15—C16	111.76 (15)
C19—O3—C20	116.7 (6)	C17—C15—C16	113.08 (17)
C1—N1—C7	104.53 (13)	N2—C15—H15	106.8
C1—N2—C2	106.11 (12)	C17—C15—H15	106.8
C1—N2—C15	125.83 (13)	C16—C15—H15	106.8
C2—N2—C15	127.75 (13)	C15—C16—H16A	109.5
N1—C1—N2	113.72 (13)	C15—C16—H16B	109.5
N1—C1—C8	122.94 (14)	H16A—C16—H16B	109.5
N2—C1—C8	123.27 (14)	C15—C16—H16C	109.5
N2—C2—C3	133.33 (15)	H16A—C16—H16C	109.5
N2—C2—C7	105.16 (13)	H16B—C16—H16C	109.5
C3—C2—C7	121.52 (15)	C18—C17—C15	113.38 (19)
C4—C3—C2	117.02 (15)	C18—C17—H17A	108.9
C4—C3—H3	121.5	C15—C17—H17A	108.9
C2—C3—H3	121.5	C18—C17—H17B	108.9
C3—C4—C5	122.30 (15)	C15—C17—H17B	108.9
C3—C4—H4	118.8	H17A—C17—H17B	107.7
C5—C4—H4	118.8	C17—C18—H18A	109.5
C6—C5—C4	120.35 (15)	C17—C18—H18B	109.5
C6—C5—C19	121.18 (16)	H18A—C18—H18B	109.5
C4—C5—C19	118.47 (15)	C17—C18—H18C	109.5
C5—C6—C7	118.24 (15)	H18A—C18—H18C	109.5
C5—C6—H6	120.9	H18B—C18—H18C	109.5
C7—C6—H6	120.9	O2—C19—O3	122.81 (18)
C6—C7—N1	128.98 (15)	O2—C19—C5	124.93 (19)
C6—C7—C2	120.55 (14)	O3—C19—C5	112.26 (15)
N1—C7—C2	110.46 (14)	C21—C20—O3	106.8 (8)
C9—C8—C13	119.04 (15)	C21—C20—H20A	110.4
C9—C8—C1	119.08 (16)	O3—C20—H20A	110.4
C13—C8—C1	121.81 (16)	C21—C20—H20B	110.4
C10—C9—C8	120.85 (19)	O3—C20—H20B	110.4
C10—C9—H9	119.6	H20A—C20—H20B	108.6
C8—C9—H9	119.6	C20—C21—H21A	109.5
C11—C10—C9	119.33 (19)	C20—C21—H21B	109.5
C11—C10—H10	120.3	H21A—C21—H21B	109.5
C9—C10—H10	120.3	C20—C21—H21C	109.5
C10—C11—C12	121.27 (17)	H21A—C21—H21C	109.5
C10—C11—H11	119.4	H21B—C21—H21C	109.5
C12—C11—H11	119.4	C20A—C21A—H21D	109.5
C11—C12—C13	119.38 (18)	C20A—C21A—H21E	109.5
C11—C12—H12	120.3	H21D—C21A—H21E	109.5
C13—C12—H12	120.3	C20A—C21A—H21F	109.5
O1—C13—C12	124.40 (17)	H21D—C21A—H21F	109.5
O1—C13—C8	115.49 (14)	H21E—C21A—H21F	109.5
C12—C13—C8	120.11 (17)	C21A—C20A—O3	101.4 (11)
O1—C14—H14A	109.5	C21A—C20A—H20C	111.5
O1—C14—H14B	109.5	O3—C20A—H20C	111.5
H14A—C14—H14B	109.5	C21A—C20A—H20D	111.5
O1—C14—H14C	109.5	O3—C20A—H20D	111.5
H14A—C14—H14C	109.5	H20C—C20A—H20D	109.3
H14B—C14—H14C	109.5

C7—N1—C1—N2	0.4 (2)	C1—C8—C9—C10	−178.21 (17)
C7—N1—C1—C8	−176.62 (16)	C8—C9—C10—C11	0.0 (3)
C2—N2—C1—N1	−1.2 (2)	C9—C10—C11—C12	0.8 (3)
C15—N2—C1—N1	−175.22 (16)	C10—C11—C12—C13	−0.5 (3)
C2—N2—C1—C8	175.86 (16)	C14—O1—C13—C12	−10.5 (3)
C15—N2—C1—C8	1.8 (3)	C14—O1—C13—C8	169.60 (17)
C1—N2—C2—C3	−178.75 (18)	C11—C12—C13—O1	179.54 (17)
C15—N2—C2—C3	−4.9 (3)	C11—C12—C13—C8	−0.6 (3)
C1—N2—C2—C7	1.37 (18)	C9—C8—C13—O1	−178.76 (16)
C15—N2—C2—C7	175.26 (16)	C1—C8—C13—O1	−1.7 (2)
N2—C2—C3—C4	180.00 (18)	C9—C8—C13—C12	1.3 (3)
C7—C2—C3—C4	−0.1 (3)	C1—C8—C13—C12	178.40 (16)
C2—C3—C4—C5	1.5 (3)	C1—N2—C15—C17	111.1 (2)
C3—C4—C5—C6	−1.5 (3)	C2—N2—C15—C17	−61.7 (2)
C3—C4—C5—C19	177.90 (17)	C1—N2—C15—C16	−121.50 (19)
C4—C5—C6—C7	0.2 (3)	C2—N2—C15—C16	65.7 (2)
C19—C5—C6—C7	−179.26 (17)	N2—C15—C17—C18	−55.0 (2)
C5—C6—C7—N1	−178.97 (17)	C16—C15—C17—C18	178.28 (19)
C5—C6—C7—C2	1.2 (3)	C20A—O3—C19—O2	−13.3 (18)
C1—N1—C7—C6	−179.38 (19)	C20—O3—C19—O2	1.3 (5)
C1—N1—C7—C2	0.5 (2)	C20A—O3—C19—C5	167.2 (17)
N2—C2—C7—C6	178.70 (16)	C20—O3—C19—C5	−178.2 (5)
C3—C2—C7—C6	−1.2 (3)	C6—C5—C19—O2	−172.8 (2)
N2—C2—C7—N1	−1.19 (19)	C4—C5—C19—O2	7.8 (3)
C3—C2—C7—N1	178.91 (16)	C6—C5—C19—O3	6.7 (3)
N1—C1—C8—C9	65.8 (2)	C4—C5—C19—O3	−172.74 (17)
N2—C1—C8—C9	−110.9 (2)	C19—O3—C20—C21	172.8 (5)
N1—C1—C8—C13	−111.2 (2)	C20A—O3—C20—C21	−86 (10)
N2—C1—C8—C13	72.0 (2)	C19—O3—C20A—C21A	119 (2)
C13—C8—C9—C10	−1.1 (3)	C20—O3—C20A—C21A	33 (6)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/N2/C1/C2/C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1ⁱ	0.93	2.56	3.471 (2)	165
C20A—H20C···Cgⁱⁱ	0.97	2.90	3.71 (4)	141

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₃
M_r	352.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.6746 (3), 12.3344 (4), 15.6158 (5)
β (°)	106.901 (1)
V (Å³)	1967.25 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.52 × 0.44 × 0.32

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.959, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	17688, 3475, 2712
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.05
No. of reflections	3475
No. of parameters	245
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.18

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1/N2/C1/C2/C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1ⁱ	0.93	2.56	3.471 (2)	165
C20A—H20C···Cgⁱⁱ	0.97	2.90	3.71 (4)	141

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

Acknowledgements

NA, HO and ASAR acknowledge the Ministry of Science, Technology and Innovations of Malaysia for funding the synthetic chemistry work under 304/PFARMASI/650544. NA thanks Universiti Sains Malaysia for the award of a postdoctoral fellowship.

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Volume 67| Part 12| December 2011| Pages o3231-o3232

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