Ethyl 2-[4-(di­methyl­amino)­phen­yl]-1-phenyl-1H-benzimidazole-5-carboxyl­ate

Yeong, K.Y.; Ali, M.A.; Choon, T.S.; Rosli, M.M.; Razak, I.A.

doi:10.1107/S1600536813012440

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o886

doi:10.1107/S1600536813012440

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Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1H-benzimidazole-5-carboxylate

Keng Yoon Yeong,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Mohd Mustaqim Rosli ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, 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: arazaki@usm.my

(Received 26 April 2013; accepted 7 May 2013; online 15 May 2013)

In the title compound, C₂₄H₂₃N₃O₂, the benzimidazole ring system makes dihedral angles of 7.28 (5) and 67.17 (5)°, respectively, with the planes of the benzene and phenyl rings, which in turn make a dihedral angle of 69.77 (6)°. In the crystal, molecules are connected by C—H⋯N and C—H⋯O interactions, forming a layer parallel to the bc plane. A π–π interaction, with a centroid–centroid distance of 3.656 (1) Å, is observed in the layer.

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002 ); Thakurdesai et al. (2007 ); McKellar & Scott (1990 ). For a related structure, see: Yoon et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₂₃N₃O₂
M_r = 385.45
Triclinic, $[P \overline 1]$
a = 8.7196 (1) Å
b = 10.4133 (2) Å
c = 11.3658 (2) Å
α = 79.312 (1)°
β = 74.393 (1)°
γ = 89.781 (1)°
V = 975.56 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.36 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.980
21016 measured reflections
5777 independent reflections
4602 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.125
S = 1.03
5777 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N2ⁱ	0.95	2.57	3.4868 (16)	164
C18—H18A⋯O2ⁱⁱ	0.95	2.50	3.2217 (17)	133
C19—H19A⋯O2ⁱⁱⁱ	0.95	2.38	3.3209 (16)	170
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+2, -y, -z+1.

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 I, global. DOI: 10.1107/S1600536813012440/is5269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012440/is5269Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012440/is5269Isup3.cml

checkCIF report

Comment top

The synthesis of benzimidazole derivatives is an active area of research in medicinal chemistry. Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as anti-HIV (Rao et al., 2002), anti-inflammatory (Thakurdesai et al., 2007) and anthelmintics (McKellar & Scott, 1990). As part of our ongoing structural studies on benzimidazole derivatives (Yoon et al., 2012), we now report the structure of the title compound.

In the title compound (Fig. 1), the benzimidazole ring (N1/N2/C1–C7) is planar with a maximum deviation of 0.025 (1) Å for atom N1. It makes dihedral angles of 7.28 (5) and 67.17 (5)°, respectively, with the benzene (C8–C13) and phenyl (C14–C19) rings, and these two rings make a dihedral angle of 69.77 (6)° with each other.

In the crystal (Fig. 2), the molecules are connected by intermolecular C15—H15A···N2ⁱ, C18—H18A···O2ⁱⁱ and C19—H19A···O2ⁱⁱⁱ interactions (Table 1) to form two-dimensional layers parallel to the bc-plane. A π–π interaction between the benzene rings of C1–C6 and C8–C13 also contributes in stabilizing the crystal structure with their centroid distances of 3.656 (1) Å (2 - x, 1 - y, 1 - z).

Related literature top

For applications of benzimidazole compounds, see: Rao et al. (2002); Thakurdesai et al. (2007); McKellar & Scott (1990). For a related structure, see: Yoon et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl 3-amino-4-(penylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-dimethylamino benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. After completion, the reaction mixture was diluted in Ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and the evaporated in vacuo to yield the product. The product was recrystallized from Ethyl acetate.

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, showing 50% probability displacement ellipsoids.
	Fig. 2. A crystal packing view of the title compound. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bonds have been omitted for clarity.

Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₄H₂₃N₃O₂	Z = 2
M_r = 385.45	F(000) = 408
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7196 (1) Å	Cell parameters from 7512 reflections
b = 10.4133 (2) Å	θ = 2.5–30.2°
c = 11.3658 (2) Å	µ = 0.09 mm⁻¹
α = 79.312 (1)°	T = 100 K
β = 74.393 (1)°	Block, yellow
γ = 89.781 (1)°	0.36 × 0.25 × 0.25 mm
V = 975.56 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5777 independent reflections
Radiation source: fine-focus sealed tube	4602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.970, T_max = 0.980	k = −14→14
21016 measured reflections	l = −15→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0552P)² + 0.401P] where P = (F_o² + 2F_c²)/3
5777 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₂₃N₃O₂	γ = 89.781 (1)°
M_r = 385.45	V = 975.56 (3) Å³
Triclinic, P1	Z = 2
a = 8.7196 (1) Å	Mo Kα radiation
b = 10.4133 (2) Å	µ = 0.09 mm⁻¹
c = 11.3658 (2) Å	T = 100 K
α = 79.312 (1)°	0.36 × 0.25 × 0.25 mm
β = 74.393 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4602 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.029
21016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
5777 reflections	Δρ_min = −0.30 e Å⁻³
265 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 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	1.34962 (11)	−0.05308 (9)	0.29082 (8)	0.02242 (19)
O2	1.18718 (12)	0.04740 (9)	0.18312 (9)	0.0266 (2)
N1	0.98249 (12)	0.30045 (9)	0.65882 (9)	0.0171 (2)
N2	0.88283 (12)	0.33970 (10)	0.49238 (9)	0.0181 (2)
N3	0.41760 (14)	0.72466 (11)	0.79245 (11)	0.0251 (2)
C1	1.05977 (14)	0.22039 (11)	0.57924 (11)	0.0166 (2)
C2	1.17590 (15)	0.12968 (11)	0.58860 (11)	0.0191 (2)
H2A	1.2151	0.1116	0.6600	0.023*
C3	1.23128 (15)	0.06738 (11)	0.48914 (11)	0.0189 (2)
H3A	1.3098	0.0043	0.4923	0.023*
C4	1.17363 (14)	0.09557 (11)	0.38285 (11)	0.0171 (2)
C5	1.05674 (14)	0.18556 (11)	0.37516 (11)	0.0173 (2)
H5A	1.0180	0.2040	0.3036	0.021*
C6	0.99820 (14)	0.24776 (11)	0.47532 (11)	0.0167 (2)
C7	0.87548 (14)	0.37009 (11)	0.60175 (11)	0.0171 (2)
C8	0.76152 (14)	0.46126 (11)	0.65582 (11)	0.0178 (2)
C9	0.67109 (15)	0.52985 (12)	0.58132 (12)	0.0205 (2)
H9A	0.6880	0.5167	0.4984	0.025*
C10	0.55857 (15)	0.61573 (12)	0.62502 (12)	0.0216 (2)
H10A	0.5000	0.6602	0.5718	0.026*
C11	0.52922 (14)	0.63840 (11)	0.74735 (12)	0.0192 (2)
C12	0.61759 (14)	0.56812 (12)	0.82302 (12)	0.0197 (2)
H12A	0.5998	0.5801	0.9064	0.024*
C13	0.72998 (14)	0.48187 (12)	0.77812 (11)	0.0193 (2)
H13A	0.7870	0.4356	0.8317	0.023*
C14	1.02675 (14)	0.31301 (11)	0.76961 (11)	0.0169 (2)
C15	1.10245 (14)	0.42822 (12)	0.77495 (12)	0.0199 (2)
H15A	1.1247	0.4994	0.7062	0.024*
C16	1.14503 (15)	0.43744 (13)	0.88256 (12)	0.0234 (3)
H16A	1.1955	0.5160	0.8879	0.028*
C17	1.11435 (16)	0.33248 (14)	0.98248 (12)	0.0251 (3)
H17A	1.1432	0.3398	1.0559	0.030*
C18	1.04162 (15)	0.21708 (13)	0.97494 (12)	0.0234 (3)
H18A	1.0224	0.1450	1.0427	0.028*
C19	0.99673 (15)	0.20678 (12)	0.86827 (11)	0.0195 (2)
H19A	0.9462	0.1282	0.8630	0.023*
C20	1.23411 (14)	0.02962 (11)	0.27581 (11)	0.0186 (2)
C21	1.40780 (16)	−0.12580 (13)	0.19169 (12)	0.0237 (3)
H21A	1.4474	−0.0649	0.1109	0.028*
H21B	1.3210	−0.1834	0.1862	0.028*
C22	1.53955 (19)	−0.20550 (18)	0.22155 (17)	0.0406 (4)
H22A	1.5714	−0.2651	0.1628	0.061*
H22B	1.5030	−0.2564	0.3065	0.061*
H22C	1.6309	−0.1474	0.2150	0.061*
C23	0.34150 (17)	0.80634 (14)	0.70882 (14)	0.0289 (3)
H23A	0.2964	0.7515	0.6638	0.043*
H23B	0.4205	0.8701	0.6492	0.043*
H23C	0.2562	0.8526	0.7569	0.043*
C24	0.41620 (17)	0.76536 (13)	0.90791 (13)	0.0260 (3)
H24A	0.3841	0.6904	0.9770	0.039*
H24B	0.3404	0.8344	0.9219	0.039*
H24C	0.5231	0.7988	0.9029	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0267 (5)	0.0233 (4)	0.0198 (4)	0.0066 (4)	−0.0075 (4)	−0.0088 (3)
O2	0.0379 (5)	0.0266 (5)	0.0194 (5)	0.0062 (4)	−0.0131 (4)	−0.0072 (4)
N1	0.0224 (5)	0.0161 (5)	0.0155 (5)	0.0039 (4)	−0.0093 (4)	−0.0038 (4)
N2	0.0211 (5)	0.0175 (5)	0.0164 (5)	0.0018 (4)	−0.0070 (4)	−0.0023 (4)
N3	0.0284 (6)	0.0242 (5)	0.0256 (6)	0.0092 (4)	−0.0107 (5)	−0.0074 (4)
C1	0.0210 (5)	0.0147 (5)	0.0148 (5)	0.0002 (4)	−0.0062 (4)	−0.0031 (4)
C2	0.0247 (6)	0.0177 (5)	0.0174 (5)	0.0034 (4)	−0.0105 (5)	−0.0028 (4)
C3	0.0237 (6)	0.0164 (5)	0.0183 (6)	0.0035 (4)	−0.0085 (5)	−0.0033 (4)
C4	0.0214 (5)	0.0144 (5)	0.0156 (5)	−0.0008 (4)	−0.0056 (4)	−0.0022 (4)
C5	0.0216 (5)	0.0173 (5)	0.0143 (5)	−0.0005 (4)	−0.0076 (4)	−0.0019 (4)
C6	0.0194 (5)	0.0146 (5)	0.0166 (5)	−0.0001 (4)	−0.0073 (4)	−0.0011 (4)
C7	0.0200 (5)	0.0145 (5)	0.0169 (5)	0.0005 (4)	−0.0072 (4)	−0.0001 (4)
C8	0.0197 (5)	0.0159 (5)	0.0179 (5)	0.0007 (4)	−0.0067 (4)	−0.0012 (4)
C9	0.0240 (6)	0.0217 (6)	0.0173 (6)	0.0036 (5)	−0.0087 (5)	−0.0034 (4)
C10	0.0232 (6)	0.0214 (6)	0.0219 (6)	0.0045 (5)	−0.0102 (5)	−0.0020 (5)
C11	0.0190 (5)	0.0167 (5)	0.0218 (6)	0.0010 (4)	−0.0060 (5)	−0.0026 (4)
C12	0.0215 (6)	0.0199 (6)	0.0180 (6)	0.0018 (4)	−0.0064 (4)	−0.0028 (4)
C13	0.0217 (6)	0.0190 (5)	0.0174 (5)	0.0021 (4)	−0.0072 (4)	−0.0013 (4)
C14	0.0195 (5)	0.0194 (5)	0.0141 (5)	0.0046 (4)	−0.0074 (4)	−0.0049 (4)
C15	0.0213 (6)	0.0193 (6)	0.0195 (6)	0.0023 (4)	−0.0053 (4)	−0.0050 (4)
C16	0.0223 (6)	0.0270 (6)	0.0240 (6)	0.0006 (5)	−0.0076 (5)	−0.0108 (5)
C17	0.0244 (6)	0.0356 (7)	0.0193 (6)	0.0040 (5)	−0.0101 (5)	−0.0095 (5)
C18	0.0254 (6)	0.0286 (6)	0.0166 (6)	0.0041 (5)	−0.0086 (5)	−0.0010 (5)
C19	0.0220 (6)	0.0187 (5)	0.0191 (6)	0.0020 (4)	−0.0084 (5)	−0.0026 (4)
C20	0.0224 (6)	0.0154 (5)	0.0178 (6)	−0.0008 (4)	−0.0053 (4)	−0.0029 (4)
C21	0.0261 (6)	0.0239 (6)	0.0218 (6)	0.0023 (5)	−0.0035 (5)	−0.0107 (5)
C22	0.0298 (7)	0.0525 (10)	0.0517 (10)	0.0160 (7)	−0.0183 (7)	−0.0301 (8)
C23	0.0271 (7)	0.0285 (7)	0.0343 (7)	0.0102 (5)	−0.0137 (6)	−0.0062 (6)
C24	0.0272 (6)	0.0243 (6)	0.0260 (7)	0.0052 (5)	−0.0054 (5)	−0.0065 (5)

Geometric parameters (Å, º) top

O1—C20	1.3478 (14)	C11—C12	1.4099 (16)
O1—C21	1.4513 (15)	C12—C13	1.3862 (17)
O2—C20	1.2127 (15)	C12—H12A	0.9500
N1—C1	1.3837 (15)	C13—H13A	0.9500
N1—C7	1.4011 (14)	C14—C15	1.3904 (17)
N1—C14	1.4404 (14)	C14—C19	1.3907 (16)
N2—C7	1.3238 (15)	C15—C16	1.3897 (17)
N2—C6	1.3866 (15)	C15—H15A	0.9500
N3—C11	1.3829 (16)	C16—C17	1.3908 (19)
N3—C24	1.4489 (17)	C16—H16A	0.9500
N3—C23	1.4500 (17)	C17—C18	1.3882 (19)
C1—C2	1.3937 (16)	C17—H17A	0.9500
C1—C6	1.4070 (16)	C18—C19	1.3923 (17)
C2—C3	1.3813 (17)	C18—H18A	0.9500
C2—H2A	0.9500	C19—H19A	0.9500
C3—C4	1.4115 (16)	C21—C22	1.491 (2)
C3—H3A	0.9500	C21—H21A	0.9900
C4—C5	1.3909 (16)	C21—H21B	0.9900
C4—C20	1.4805 (17)	C22—H22A	0.9800
C5—C6	1.3908 (17)	C22—H22B	0.9800
C5—H5A	0.9500	C22—H22C	0.9800
C7—C8	1.4653 (16)	C23—H23A	0.9800
C8—C13	1.3995 (17)	C23—H23B	0.9800
C8—C9	1.4069 (16)	C23—H23C	0.9800
C9—C10	1.3802 (17)	C24—H24A	0.9800
C9—H9A	0.9500	C24—H24B	0.9800
C10—C11	1.4087 (18)	C24—H24C	0.9800
C10—H10A	0.9500

C20—O1—C21	115.44 (10)	C8—C13—H13A	119.2
C1—N1—C7	106.59 (9)	C15—C14—C19	121.28 (11)
C1—N1—C14	122.51 (9)	C15—C14—N1	120.01 (10)
C7—N1—C14	130.52 (10)	C19—C14—N1	118.68 (11)
C7—N2—C6	105.79 (10)	C16—C15—C14	118.87 (11)
C11—N3—C24	119.19 (11)	C16—C15—H15A	120.6
C11—N3—C23	119.82 (11)	C14—C15—H15A	120.6
C24—N3—C23	117.76 (11)	C15—C16—C17	120.50 (12)
N1—C1—C2	131.70 (11)	C15—C16—H16A	119.8
N1—C1—C6	105.58 (10)	C17—C16—H16A	119.8
C2—C1—C6	122.72 (11)	C18—C17—C16	120.03 (12)
C3—C2—C1	116.81 (11)	C18—C17—H17A	120.0
C3—C2—H2A	121.6	C16—C17—H17A	120.0
C1—C2—H2A	121.6	C17—C18—C19	120.16 (12)
C2—C3—C4	121.33 (11)	C17—C18—H18A	119.9
C2—C3—H3A	119.3	C19—C18—H18A	119.9
C4—C3—H3A	119.3	C14—C19—C18	119.14 (12)
C5—C4—C3	121.25 (11)	C14—C19—H19A	120.4
C5—C4—C20	117.45 (10)	C18—C19—H19A	120.4
C3—C4—C20	121.30 (11)	O2—C20—O1	122.55 (11)
C6—C5—C4	118.08 (10)	O2—C20—C4	124.51 (11)
C6—C5—H5A	121.0	O1—C20—C4	112.95 (10)
C4—C5—H5A	121.0	O1—C21—C22	107.42 (11)
N2—C6—C5	130.04 (11)	O1—C21—H21A	110.2
N2—C6—C1	110.18 (10)	C22—C21—H21A	110.2
C5—C6—C1	119.77 (11)	O1—C21—H21B	110.2
N2—C7—N1	111.84 (10)	C22—C21—H21B	110.2
N2—C7—C8	122.37 (10)	H21A—C21—H21B	108.5
N1—C7—C8	125.72 (11)	C21—C22—H22A	109.5
C13—C8—C9	116.88 (11)	C21—C22—H22B	109.5
C13—C8—C7	125.18 (11)	H22A—C22—H22B	109.5
C9—C8—C7	117.88 (11)	C21—C22—H22C	109.5
C10—C9—C8	122.03 (12)	H22A—C22—H22C	109.5
C10—C9—H9A	119.0	H22B—C22—H22C	109.5
C8—C9—H9A	119.0	N3—C23—H23A	109.5
C9—C10—C11	121.03 (11)	N3—C23—H23B	109.5
C9—C10—H10A	119.5	H23A—C23—H23B	109.5
C11—C10—H10A	119.5	N3—C23—H23C	109.5
N3—C11—C10	121.81 (11)	H23A—C23—H23C	109.5
N3—C11—C12	121.07 (11)	H23B—C23—H23C	109.5
C10—C11—C12	117.11 (11)	N3—C24—H24A	109.5
C13—C12—C11	121.30 (11)	N3—C24—H24B	109.5
C13—C12—H12A	119.4	H24A—C24—H24B	109.5
C11—C12—H12A	119.4	N3—C24—H24C	109.5
C12—C13—C8	121.63 (11)	H24A—C24—H24C	109.5
C12—C13—H13A	119.2	H24B—C24—H24C	109.5

C7—N1—C1—C2	−179.19 (12)	C8—C9—C10—C11	−0.05 (19)
C14—N1—C1—C2	7.2 (2)	C24—N3—C11—C10	−166.84 (12)
C7—N1—C1—C6	1.38 (12)	C23—N3—C11—C10	−7.59 (19)
C14—N1—C1—C6	−172.24 (10)	C24—N3—C11—C12	13.84 (18)
N1—C1—C2—C3	−178.49 (12)	C23—N3—C11—C12	173.09 (12)
C6—C1—C2—C3	0.86 (18)	C9—C10—C11—N3	179.62 (12)
C1—C2—C3—C4	0.58 (18)	C9—C10—C11—C12	−1.04 (18)
C2—C3—C4—C5	−1.15 (18)	N3—C11—C12—C13	−179.78 (12)
C2—C3—C4—C20	179.44 (11)	C10—C11—C12—C13	0.87 (18)
C3—C4—C5—C6	0.24 (17)	C11—C12—C13—C8	0.40 (19)
C20—C4—C5—C6	179.67 (10)	C9—C8—C13—C12	−1.47 (18)
C7—N2—C6—C5	−178.08 (12)	C7—C8—C13—C12	−178.60 (11)
C7—N2—C6—C1	1.17 (13)	C1—N1—C14—C15	108.78 (13)
C4—C5—C6—N2	−179.65 (11)	C7—N1—C14—C15	−63.17 (17)
C4—C5—C6—C1	1.16 (17)	C1—N1—C14—C19	−69.23 (15)
N1—C1—C6—N2	−1.61 (13)	C7—N1—C14—C19	118.82 (13)
C2—C1—C6—N2	178.89 (11)	C19—C14—C15—C16	−1.54 (18)
N1—C1—C6—C5	177.73 (10)	N1—C14—C15—C16	−179.49 (11)
C2—C1—C6—C5	−1.76 (18)	C14—C15—C16—C17	0.87 (19)
C6—N2—C7—N1	−0.27 (13)	C15—C16—C17—C18	0.43 (19)
C6—N2—C7—C8	−177.42 (10)	C16—C17—C18—C19	−1.10 (19)
C1—N1—C7—N2	−0.73 (13)	C15—C14—C19—C18	0.88 (18)
C14—N1—C7—N2	172.19 (11)	N1—C14—C19—C18	178.86 (11)
C1—N1—C7—C8	176.31 (11)	C17—C18—C19—C14	0.45 (19)
C14—N1—C7—C8	−10.77 (19)	C21—O1—C20—O2	−3.58 (17)
N2—C7—C8—C13	169.33 (11)	C21—O1—C20—C4	176.91 (10)
N1—C7—C8—C13	−7.41 (19)	C5—C4—C20—O2	−1.07 (18)
N2—C7—C8—C9	−7.78 (17)	C3—C4—C20—O2	178.36 (12)
N1—C7—C8—C9	175.48 (11)	C5—C4—C20—O1	178.43 (10)
C13—C8—C9—C10	1.30 (18)	C3—C4—C20—O1	−2.14 (16)
C7—C8—C9—C10	178.65 (11)	C20—O1—C21—C22	177.00 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N2ⁱ	0.95	2.57	3.4868 (16)	164
C18—H18A···O2ⁱⁱ	0.95	2.50	3.2217 (17)	133
C19—H19A···O2ⁱⁱⁱ	0.95	2.38	3.3209 (16)	170

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₃O₂
M_r	385.45
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.7196 (1), 10.4133 (2), 11.3658 (2)
α, β, γ (°)	79.312 (1), 74.393 (1), 89.781 (1)
V (Å³)	975.56 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	21016, 5777, 4602
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.125, 1.03
No. of reflections	5777
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C15—H15A···N2ⁱ	0.95	2.57	3.4868 (16)	164
C18—H18A···O2ⁱⁱ	0.95	2.50	3.2217 (17)	133
C19—H19A···O2ⁱⁱⁱ	0.95	2.38	3.3209 (16)	170

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors would like to express their gratitude to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine and Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia. This work was funded through Research Grant No. RUC (1001/PSK/8620012) and HiCoE Research Grant No (311/CIPPM/4401005). IAR also thanks USM for the Short Term Grant, No. 304/PFIZIK/6312078.

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